Herbicidal composition comprising pretilachlor or pyriftalid with sulfonylureas

ABSTRACT

Liquid herbicidal composition, containing a grass herbicide that is suspended or dissolved in a non-aqueous liquid phase, a herbicide of the sulfonylurea type that is suspended in a non-aqueous liquid phase, and at least one surface-active substance.

This application is a continuation of Ser. No. 09/849,817, filed May 4, 2001 Abandoned.

The present invention relates to a new liquid herbicidal composition, the preparation thereof, as well as the use of the composition in the control of undesired plant growth in crops of cultivated plants.

According to the present invention, a liquid herbicidal composition is proposed, which contains, in addition to customary formulation excipients, (a) at least one grass herbicide that is suspended or dissolved in a non-aqueous liquid phase, (b) at least one herbicide of the sulfonylurea type that is suspended in a non-aqueous liquid phase, and (c) at least one non-ionic or anionic, surface-active substance or a mixture of the non-ionic and anionic substances.

Grass herbicides which may be used in accordance with the invention belong especially to the chemical classes of acetanilides, phenoxypropionic acids, pyrimidinyloxybenzoic acids, phenylsulfonyltriazoles, oxyacetamides, oxazolidindiones, phenylbenzamides, pyrimidinyl thiophthalides and indanes, and are preferably pretilachlor, cyhalofop, pyriminobac, cafenstrole, mefenacet, fentrazamid, oxaziclomefon, pentoxazone, etobenzanid, indanofan as well as epoprodan and the compound of formula I

These grass herbicides may also be used in a mixture together. They exist in dissolved or dispersed form in a non-aqueous liquid phase. The herbicides of the sulfonylurea type are also dispersed in preferably the same non-aqueous liquid phase. These are preferably cinosulfuron, pyrazosulfuron, bensulfuron, azimsulfuron, imazosulfuron, ethoxysulfuron, cyclosulfamuron or halosulfuron or mixtures thereof.

The preferred non-aqueous liquid phases include all vegetable and mineral oils, such as rapeseed oil, soybean oil, sunflower oil, castor oil, pine oil, cottonseed oil, as well as derivatives of these oils, for example esters, especially methylesters of these oils, as well as paraffinic and aromatic mineral oils, such as Orchex 796, Shellsol types, Isopar types, aromatic fractions, such as Solvesso 200 and esters such as Exxate 700, as well as mixtures thereof.

The non-ionic and anionic surface-active substances may be conventional, commercially available substances, for example ethoxylated vegetable oils such as Emulsogen EL, ethoxylated fat alcohols such as Genapol O-050, ethoxylated alkylphenols such as Synperonic NP8, ethoxylated polyethylene glycols or polypropylene glycols, e.g. Pluronic types, ethoxylated tristyrylphenol derivatives such as Soprophor 4D384 or Soprophor S/25, oleyl polyglycol ethers such as Genapol U-050, and silicone surfactants such as Silwet L77, as well as dodecylbenzene sulfonates such as Sermul 88A, alcohol ether sulfonates such as Genapol LRO, lignin sulfonates such as Ultrazin NA, phenol sulfonates such as Sipragil GN and polycarboxylates such as Geropon TA72, sulfonated naphthalene/formaldehyde condensates such as Supragil MSN, sulfosuccinates such as Aerosol OT 70 PG, polyacrylate derivatives such as Atlox 4913, maleic acid/olefin copolymers such as Sokolan CP9, alkyl polyglycosides, alkyl succinic acid anhydride derivatives, sorbitan esters, ethoxylated sorbitan esters, alkyl and alkylaryl polyglycol ether phosphoric acid esters and ethoxylated fatty acid esters, as well as taurides such as Hostapon T hk.

The above-mentioned herbicides are described in the Pesticide Manual, Eleventh Edition, British Crop Protection Council, 1997. The compound of formula I is known from EP-A-447506, fentrazamid from British Crop Protection Conference Proceedings, 1997, 67-72, and oxaziclomefon from British Crop Protection Conference Proceedings, 1997, 73-80.

Preferred herbicidal compositions according to the present invention contain as the grass herbicide cyhalofop, pyriminobac, cafenstrole, mefenacet, fentrazamid, oxaziclomefon, pentoxazone, etobenzanid, indanofan, epoprodan, pretilachlor or a compound of formula I

or mixtures thereof.

As the herbicide of the sulfonylurea type, the compositions according to the invention preferably contain pyrazosulfuron, bensulfuron, azimsulfuron, imazosulfuron, ethoxysulfuron, cyclosulfamuron, halosulfuron or cinosulfuron or mixtures thereof.

The non-aqueous liquid phases to be used are preferably mineral oils or vegetable oils, or also mixtures thereof. The preferred non-ionic, surface-active substances that may be considered are ethoxylated vegetable oil, ethoxylated fat alcohol, ethoxylated alkylphenol, ethoxylated polyethylene glycol and polypropylene glycol and copolymers thereof, ethoxylated tristyrylphenol derivative, oleyl polyglycol ether or silicone surfactant, and the anionic surface-active substance may be a dodecylbenzene sulfonate, sulfosuccinate, ethoxylated tristyrylphenol sulfate or phosphate, alcohol ether sulfonate, lignin sulfonate, ethoxylated phenol sulfonate or polycarboxylate.

A significant composition is one which contains as the grass herbicide pretilachlor or the compound of formula I or a mixture thereof suspended or dissolved in a vegetable oil, as the herbicide of the sulfonylurea type bensulfuron, pyrazosulfuron, azimsulfuron, imazosulfuron or cinosulfuron or mixtures thereof suspended in a vegetable oil, and as the surface-active substance a mixture of non-ionic and anionic compounds. Of these, preference is given to a composition which contains as the grass herbicide the compound of formula I suspended or dissolved in a vegetable oil, as the herbicide of the sulfonylurea type cinosulfuron suspended in a vegetable oil, and as the surface-active substance a mixture of non-ionic and anionic compounds. Of these, further preference is given to a composition which contains as the grass herbicide pretilachlor suspended or dissolved in a vegetable oil, as the herbicide of the sulfonylurea type cinosulfuron suspended in a vegetable oil, and as the surface-active substance a mixture of non-ionic and anionic compounds.

An especially effective composition contains as the grass herbicide pretilachlor or the compound of formula I or a mixture thereof, preferably the compound of formula I alone, suspended or dissolved in rapeseed oil or rapeseed oil methyl ester or in a mixture thereof, as the herbicide of the sulfonylurea type bensulfuron suspended in rapeseed oil or rapeseed oil methyl ester or in a mixture thereof, and as the surface-active substance a mixture of a non-ionic with an anionic compound selected from castor oil ethoxylate, dodecylbenzene sulfonate, ethoxylated tristyrylphenol sulfate and oleyl polyglycol ether.

The compositions according to the invention have the great advantage that they may contain the herbicidal active ingredients in high concentrations, and that they remain protected from decomposition over a longer period of time. They also offer the possibility that other oil-soluble or liquid admixtures may be added without problems, such as additives that are suitable for increasing the biological activity, as well as stabilisers such as epoxidised vegetable oils. Surprisingly, the compositions according to the invention show practically no damage to the crops of cultivated plants after their application, despite using organic liquids.

The compositions according to the invention are preferably suitable for the control of weeds in flooded paddy fields. The process is advantageously carried out in such a way that the required amount of composition is mixed with the same amount or up to ten times the amount of water, and applied directly to the already flooded paddy field, or is added to the water flowing in during flooding of the paddy field (so-called splash application). Furthermore, it is also possible, to apply the composition dropwise or in portions simultaneously with the mechanical planting of the rice plants (so-called dip application). Spray application of the composition according to the invention is similarly possible, but requires a higher dilution with water.

The application rates of composition according to the invention may vary within a wide range. It is preferable to use 50 to 2000 g/ha herbicide (grass herbicide plus herbicide of the sulfonylurea type).

The liquid compositions according to the invention contain per liter preferably 30 to 1920 g grass herbicide and 20 to 80 g herbicide of the sulfonylurea type, as well as 50 to 300 g of surface-active substance (anionic plus non-ionic). Normally, 2-20 I/ha of the formulations described below by way of example are required for direct application or for splash application. For spray application, this amount is usually 20-500 I/ha. The compositions according to the invention may also contain further customary additives, for example inert carriers such as kaolin and chalk, stabilisers, anti-foaming agents, preservatives, viscosity regulators, thickeners such as silicic acid or bentonite, binders, tackifiers, as well as fertilisers or other active ingredients. The compositions are produced in known manner, e.g. by intimately mixing and/or grinding the active ingredients with the formulation excipients and with liquid or solid carriers. Particularly preferred formulations are made up as follows:

FORMULATION EXAMPLES

Substance Trade name function conc. g/l F1: Compound of active ingredient 180 formula I pretilachlor Rifit, Solnet active ingredient 180 bensulfuron Londax active ingredient  51 methyl castor oil Alkamuls R/81 surface-active  80 ethoxylate 18EO substance dodecylbenzene Sermul EA88 surface-active  50 sulfonate substance rapeseed oil Edenor ME-SU non-aqueous liquid  20 methyl ester phase rapeseed oil non-aqueous liquid remainder phase to make up 1 l F2: Compound of active ingredient 180 formula I pretilachlor Rifit, Solnet active ingredient 180 bensulfuron Londax active ingredient  51 methyl ethoxylated Soprophor 4D384 surface-active  20 tristyryiphenol substance sulfate dodecylbenzene Sermul EA88 surface-active  40 sulfonate substance oleyl polyglycol Genapol U-050 surface-active  90 ether substance mineral oil Orchex 796 non-aqueous liquid remainder phase to make up 1 l F3: Compound of active ingredient 180 formula I pretilachlor Rifit, Solnet active ingredient 180 bensulfuron Londax active ingredient  51 methyl ethoxylated Soprophor 4D384 surface-active  20 tristyrylphenol substance sulfate dodecylbenzene Sermul EA88 surface-active  50 sulfonate substance castor oil Alkamuls R/81 surface-active  80 ethoxylate 18EO substance rapeseed oil Edenor ME-SU non-aqueous liquid remainder methyl ester phase to make up 1 l F4: Compound of active ingredient 180 formula I pretilachlor Rifit, Solnet active ingredient 180 bensulfuron Londax active ingredient  51 methyl castor oil Marlowet LVS surface-active 150 derivative substance rapeseed oil non-aqueous liquid remainder phase to make up 1 l F5: Compound of active ingredient 180 formula I pretilachlor Rifit, Solnet active ingredient 180 bensulfuron Londax active ingredient  30 methyl azimsulfuron Gulliver active ingredient  6 dodecylbenzene Sermul EA88 surface-active  50 sulfonate substance castor oil Sermul EN24 surface-active  50 ethoxylate substance silicic acid Aerosil 200 thickener  20 rapeseed oil non-aqueous liquid 234 phase rapeseed oil Agrimul 2232 F non-aqueous liquid remainder methyl ester phase to make up 1 l F6: Compound of active ingredient 180 formula I pretilachlor Rifit, Solnet active ingredient 180 bensulfuron Londax active ingredient  30 methyl azimsulfuron Gulliver active ingredient  6 dodecylbenzene Sermul EA88 surface-active  65 sulfonate substance castor oil Sermul EN24 surface-active  65 ethoxylate substance tristyrylphenol Soprophor BSU surface-active  20 ethoxylate substance silicic acid Aerosil 200 thickener  30 rapeseed oil non-aqueous liquid 174 phase rapeseed oil Agrimul 2232 F non-aqueous liquid remainder methyl ester phase to make up 1 l F7: Compound of active ingredient 180 formula I cinosulfuron Setoff active ingredient  24 ethoxylated Soprophor 4D384 surface-active  20 tristyrylphenol substance sulfate castor oil Sermul EN24 surface-active  40 ethoxylate substance dodecylbenzene Sermul EA88 surface-active  40 sulfonate substance silicic acid Aerosil 200 thickener  40 rapeseed oil Agrimul 2232 F non-aqueous liquid remainder methyl ester phase to make up 1 l F8: Compound of active ingredient 180 formula I cinosulfuron Setoff active ingredient  24 ethoxylated Soprophor 4D384 surface-active  20 tristyrylphenol substance sulfate castor oil Sermul EN24 surface-active  65 ethoxylate substance dodecylbenzene Sermul EA88 surface-active  65 sulfonate substance silicic acid Aerosil 200 thickener  40 aluminium Attagel 50 inert carrier  30 silicate rapeseed oil Agrimul 2232 F non-aqueous liquid remainder methyl ester phase to make up 1 l F9: pretilachlor Rifit active ingredient 450 cinosulfuron Setoff active ingredient  24 ethoxylated Soprophor 4D384 surface-active  20 tristyrylphenol substance sulfate castor oil Sermul EN24 surface-active  60 ethoxylate substance dodecylbenzene Sermul EA88 surface-active  60 sulfonate substance aluminium Kaolin inert carrier 250 silicate silicic acid Aerosil 200 thickener  30 rapeseed oil Agrimul 2232 F non-aqueous liquid remainder methyl ester phase to make up 1 l F10: pretilachlor Rifit active ingredient 450 cinosulfuron Setoff active ingredient  24 ethoxylated Soprophor 4D384 surface-active  20 tristyrylphenol substance sulfate castor oil Sermul EN24 surface-active  60 ethoxylate substance dodecylbenzene Sermul EA88 surface-active  60 sulfonate substance aluminium Kaolin inert carrier 200 silicate silicic acid Aerosil 200 thickener  30 rapeseed oil Agrimul 2232 F non-aqueous liquid remainder methyl ester phase to make up 1 l

APPLICATION EXAMPLES

Formulations F1, F2, F3, F4, F5, F6, F7, F8, F9 and F10 are diluted with water to 5 liters, and introduced directly to a flooded paddy field at an application rate of 5 l/ha (splash application). 22 days after application, control of the weeds Echinochloa, Scirpus and Monochoria is investigated, as well as the phytotoxic activity of the compositions on rice (100% indicates complete control of the weeds or completely withered rice, 0% indicates no control of the weeds or no phytotoxic activity on the rice). This takes place in tests running in parallel: a) upon emergence, b) at the 2.5 leaf stage and c) at the 4.1 leaf stage of Echinochloa. The results obtained in these tests are summarised in the following Table:

% weed control % phytotoxic activity Formulation a) b) c) F1 rice 0 5 11 Echinochloa 99 96 95 Scirpus 98 92 94 Monochoria 100 95 95 F2 rice 0 7 9 Echinochloa 99 98 92 Scirpus 98 94 94 Monochoria 100 94 93 F3 rice 3 8 9 Echinochloa 100 95 93 Scirpus 99 90 95 Monochoria 100 89 96 F5 rice 0 0 Echinochloa 100 70 Scirpus 90 80 Monochoria 95 90 F6 rice 0 0 Echinochloa 100 80 Scirpus 90 80 Monochoria 98 90 F7 rice 0 0 Echinochloa 98 70 Scirpus 70 80 Monochoria 90 90 F8 rice 0 0 Echinochloa 98 70 Scirpus 70 90 Monochoria 95 90 F9 rice 0 0 Echinochloa 100 20 Scirpus 98 90 Monochoria 100 95 F10 rice 0 0 Echinochloa 100 10 Scirpus 95 90 Monochoria 100 90 The same results are obtained if these formulations are diluted with water, e.g. to 2-500 l. 

What is claimed is:
 1. Liquid herbicidal composition, containing (a) at least one grass herbicide that is suspended or dissolved in a vegetable or mineral oil or a mixture of these oils, said grass herbicide comprising at least one member selected from the group consisting of the compound of formula (I),

 pretilachlor and mixtures thereof, (b) at least one herbicide of the sulfonylurea type that is suspended in a vegetable or mineral oil or a mixture of these oils, and (c) at least one non-ionic or anionic, surface-active substance or a mixture of the non-ionic and anionic surface-active substances.
 2. Composition according to claim 1, containing as the herbicide of the sulfonylurea type pyrazosulfuron, bensulfuron, azimsulfuron, imazosulfuron, ethoxysulfuron, cyclosulfamuron, halosulfuron or cinosulfuron or a mixture thereof.
 3. Composition according to claim 1, containing as the vegetable or mineral oil at least one member selected from the group consisting of rapeseed oil, soybean oil, sunflower oil, castor oil, pine oil, cottonseed oil, including derivatives of these oils, paraffinic mineral oils and aromatic mineral oils.
 4. Composition according to claim 1, containing as the non-ionic, surface-active substance, an ethoxylated vegetable oil, ethoxylated fat alcohol, ethoxylated alkylphenol, ethoxylated polyethylene glycol or propylene glycol or copolymers thereof, ethoxylated tristyrylphenol derivative, oleyl polyglycol ether or silicone surfactant, or as the anionic surface-active substance, a dodecylbenzene sulfonate, sulfosuccinate, ethoxylated tristyrylphenol sulfate or phosphate, alcohol ether sulfonate, lignin sulfonate, ethoxylated phenol sulfate or polycarboxylate or a mixture of these non-ionic and anionic, surface-active compounds.
 5. Composition according to claim 1, containing as the grass herbicide pretilachlor or the compound of formula I or a mixture thereof suspended or dissolved in a vegetable oil, as the herbicide of the sulfonylurea type bensulfuron, pyrazosulfuron, azimsulfuron, imazosulfuron or cinosulfuron or mixtures thereof suspended in a vegetable oil, and as the surface-active substance a mixture of non-ionic and anionic compounds, selected from the group consisting of ethoxylated vegetable oil, ethoxylated fat alcohol, ethoxylated alkylphenol, ethoxylated polyethylene glycol or propylene glycol or copolymers thereof, ethoxylated tristyrylphenol derivative, oleyl polyglycol ether and silicone surfactant, dodecylbenzene sulfonate sulfosuccinate, ethoxylated tristyrylphenol sulfate or phosphate, alcohol ether sulfonate, lignin sulfonate, ethoxylated phenol sulfate and polycarboxylate.
 6. Composition according to claim 5, containing as the grass herbicide the compound of formula I and as the herbicide of the sulfonylurea type cinosulfuron.
 7. Composition according to claim 5, containing as the grass herbicide pretilachlor and as the herbicide of the sulfonylurea type cinosulfuron.
 8. Composition according to claim 5, containing as the grass herbicide pretilachlor or the compound of formula I or a mixture thereof, suspended or dissolved in rapeseed oil or rapeseed oil methyl ester or in a mixture thereof, as the herbicide of the sulfonylurea type bensulfuron suspended in rapeseed oil or rapeseed oil methyl ester or in a mixture thereof, and as the surface-active substance a mixture of a non-ionic with an anionic compound selected from castor oil ethoxylate, dodecylbenzene sulfonate, ethoxylated tristyrylphenol sulfate and oleyl polyglycol ether.
 9. Composition according to claim 8, containing as the grass herbicide the compound of formula I.
 10. A method for controlling undesired plant growth in rice crops said method comprising direct application of the composition of claim 1 to already flooded paddy fields, to paddy fields that are just being flooded, or during planting of the rice plants. 